Shelter Island Vacations from ₩808,376

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Seville Nomad, in the Unbound Collection by Hyatt
Hyatt Centric Times Square New York
Hilton Club The Quin New York
NobleDEN Hotel
Thompson Central Park New York, by Hyatt

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ₩113,462 per night from Oct 19 to Oct 20
₩113,462
₩130,488 total
Oct 19 - Oct 20
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"

Reviewed on Oct 11, 2025

Pier Blue Inn Old Saybrook - Essex
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is ₩419,641 per night from Nov 4 to Nov 5
₩419,641
₩572,738 total
Nov 4 - Nov 5
includes taxes & fees
8.2/10 Very Good! (670 reviews)
"We had a lovely one night stay. Everyone was very friendly. Having my dogs there was a treat. The spa was great and relaxing. GIGI’s restaurant is a must. The only complaint I have is that the bedclothes need to be updated. They were torn/frayed in multiple places. Other than that it was a great ..."

Reviewed on Oct 11, 2025

Gurney's Montauk Resort & Seawater Spa
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ₩132,444 per night from Nov 2 to Nov 3
₩132,444
₩152,311 total
Nov 2 - Nov 3
includes taxes & fees
7.6/10 Good! (1,008 reviews)
"Our stay was just what we needed. Breakfast was full of choices and and plenty to eat and drink. A perfect stop in a lovely town."

Reviewed on Oct 12, 2025

Quality Inn Old Saybrook - Westbrook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.